Geena Davis
Event: 64th Academy Awards
Year: 1992
Est. Cost: $10,000*
Geena Davis’s choice for the 1992 Oscars was a ruffled satin dress with a large bow at the back. The gown, which featured a short front and a long train, was criticized for its strange cut and proportions. The overly voluminous skirt and the unflattering neckline made it one of the most expensive red carpet fails in history.